Heminigerone

Base Information

• Chemical Name: Heminigerone
• CAS No.: 17276-15-2
• Molecular Formula: C16H14O5
• Molecular Weight: 286.2794
• UNII: TLJ90R747F
• DSSTox Substance ID: DTXSID50169393
• Nikkaji Number: J14.298K
• Wikidata: Q27290019
• Metabolomics Workbench ID: 137228
• ChEMBL ID: CHEMBL469613
• Mol file: 17276-15-2.mol

Synonyms:Heminigerone;Rubrofusarin B;TMD 256a2;TMD-256a2;17276-15-2;UNII-TLJ90R747F;CHEMBL469613;TLJ90R747F;5-hydroxy-6,8-dimethoxy-2-methylbenzo[g]chromen-4-one;4H-Naphtho(2,3-b)pyran-4-one, 5-hydroxy-6,8-dimethoxy-2-methyl-;rubrofusarin monomethyl ether;SCHEMBL16227248;DTXSID50169393;CHEBI:133805;BDBM50241852;Q27290019;5-hydroxy-6,8-dimethoxy-2-methyl-benzo[g]chromen-4-one;5-HYDROXY-6,8-DIMETHOXY-2-METHYL-4H-BENZO[G]CHROMEN-4-ONE;5-hydroxy-6,8-dimethoxy-2-methyl-4H-naphtho(2,3-b)pyran-4-one

Chemical Property of Heminigerone

Chemical Property:

• Vapor Pressure: 3.21E-10mmHg at 25°C
• Boiling Point: 489.8°Cat760mmHg
• Flash Point: 185.2°C
• PSA: 68.90000
• Density: 1.327g/cm³
• LogP: 2.97740
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 286.08412354
• Heavy Atom Count: 21
• Complexity: 446

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C2=C(C3=C(C=C(C=C3C=C2O1)OC)OC)O

Technology Process of Heminigerone

There total 3 articles about Heminigerone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 17.0%

methyl 2,4-dimethoxy-6-[(6-methyl-4-oxo-4H-pyran-2-yl)methyl]benzoate (67985-14-2) → rubrofusarin B (17276-15-2)

Guidance literature:

With trityllithium; In tetrahydrofuran; at -15 ℃; for 1h;

Reference yield:

methyl 2,4-dimethoxy-6-methylbenzoate (6110-37-8) → rubrofusarin B (17276-15-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium di-isopropylamide, 2.) benzyl-lithium, lithium di-isopropylamide / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 2.5 h

2: 17 percent / trityl-lithium / tetrahydrofuran / 1 h / -15 °C

With trityllithium; benzyllithium; lithium diisopropyl amide; In tetrahydrofuran;

Reference yield:

→ rubrofusarin B (17276-15-2)

Guidance literature:

aus 2-Acetyl-6,8-dimethoxy-naphthalin-1,3-diol, 1) E., NaH zuletzt bei Siedetemp., 2) konz. HCl in Me. ;

upstream raw materials:

methyl 2,4-dimethoxy-6-[(6-methyl-4-oxo-4H-pyran-2-yl)methyl]benzoate

methyl 2,4-dimethoxy-6-methylbenzoate

Downstream raw materials:

ustilaginoidin A

isoustilaginoidin A

Nor-rubrofusarin